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Title: Combinatorial approach towards synthesis of 2',3'-dideoxynucleosides and enzyme-catalysed selective hydrolysis of diethyl acetamidomalonate and amides of polyacetoxy aromatic carboxylic acid
Authors: Kumar, Ajay
Singh, Amarjit
Kumar, Rajesh
Prasad, Ashok K
Parmar, Virinder S
Tararov, Vitali I
Belokon, Yuri N
Singh, Sanjay K
Wengel, Jesper
Issue Date: Jun-1997
Publisher: NISCAIR-CSIR, India
Abstract: Seventeen noveI 3’-alkylthio-2’,3’-dideoxynucleosides have been synthesised by Michael-type addition of alkylthiols to an ,α,β-unsaturated hexose aldehyde, followed by acetylation, nucleoside coupling and deprotection. Based on these results, a general scheme for combinatorial synthesis of libraries of 3’-substituted 2’,3’-dideoxynucleosides has been proposed. Porcine pancreatic lipase (PPL) has been found to hydrolyse the amides of polyacetoxyaromatic carboxylic acids in a highly chemoselective fashion. The enzyme exclusively hydrolyses the ester group over the amide group. Hydrolysis of diethyl acetamidomalonate in phosphate buffer in the presence of α-chymotrypsin proceeds enantioselectively affording the (+)-monoacid.
Page(s): 507-512
ISSN: 0975-0975(Online); 0376-4710(Print)
Appears in Collections:IJC-A Vol.36A(06) [June 1997]

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